The song tells of a teenage romance and first sexual experience with a girl who wears the titular hat. According to watchmojo.com, this was inspired by a deleted scene from Purple Rain, where The Kid and Apollonia made love in a barn. The video for the song was directed primarily by himself, with animation created by Colossal Pictures co-founder Drew Takahashi. The extended version was included on Ultimate in 2006. While the song hit number 1 in Cash Box and reached number 2 on the Billboard Hot 100 in the US, behind "A View to a Kill" by Duran Duran, it reached only number 25 on the UK Singles Chart.